Use of dichlorophthaloyl (DCPhth) group as an amino protecting group in oligosaccharide synthesis

Tetrahedron

Volumn 54, Issue 8, 1998, Pages 1381-1394

  Lergenmüller, Matthias ^a   Ito, Yukishige ^a   Ogawa, Tomoya ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4,5 DICHLOROPHTHALOYL GROUP; ALCOHOL; ASPARAGINE; DISACCHARIDE; ETHYLENEDIAMINE; GLUCOSAMINE; GLYCOPROTEIN; GLYCOSIDE; MONOSACCHARIDE; N ACETYLGLUCOSAMINE; OLIGOSACCHARIDE; SOLVENT; TRISACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DEACETYLATION; GLYCOSYLATION; PRIORITY JOURNAL; SYNTHESIS; TECHNIQUE;

EID: 0032546088     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10377-5     Document Type: Article

References (21)

1. 1. Alternative address: Graduate School of Agriculture and Life Science, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo 113 Japan
2. 2. Banoub, J.; P. Boullanger, P.; Lafont, D. Chem. Rev., 1992, 92, 1167.
3. 3. Debenham, J.; R. Rodebaugh, R.; Fraser-Reid, B. Liebigs Ann. 1997, 791.
4. 4. Lemieux, R. U.; Takeda T.; Chung, B. Y. ACS Symo. Ser., 1976, 39, 90.
5. 5. Shimizu, H.; Ito, Y.; Matsuzaki, Y.; Iijima, H; Ogawa, T. Biosci. Biotech. Biochem. 1996, 60, 73.
6. 6. Bergmann, M.; Zervas, L. Ber., 1931, 64, 975.
7. 7. Fukuyama, T.; Laird A. A.; Hotchkiss, L. M. Tetrahedron Lett., 1985, 26, 6291.
8. 8. Koeners, H. L.; Verhoeven, J.; van Boom, J. H. Receil Trav. Chim. Pays-Bas, 1981, 100, 65.
9. 9. Anet, E. F. L. J. Carbohydr. Res. 1968, 7, 84-85; Pannecoucke, X.; Schmitt G.; Luu, B. Tetrahedron 1994, 50, 6569.
10. 9. Anet, E. F. L. J. Carbohydr. Res. 1968, 7, 84-85; Pannecoucke, X.; Schmitt G.; Luu, B. Tetrahedron 1994, 50, 6569.
11. 10. Relatively strong conditions are required presumably due to the steric hindrance of 4-OAc group. NMR analysis of crude mixture suggested that partial destruction of the DCPhth group occurred.
12. 11. Glaudmans, C. P. J.; Berotolini, M. in Methods in Carbohydrate Chem., Vol. VIII, 271-275, Academic Press, N.Y. (1970).
13. 12. (a) Hasegawa, A.; Nagahama, T.; Ohki, H.; Hotta, K.; Ishida, H.; M. Kiso, M. J. Carbohydr. Chem., 1991, 10, 493.
14. (b) Hasegawa, A.; Ohki, H.; Nagahama, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 1991, 212, 277.
15. 13. (a) Komba, S.; Ishida, H.; Kiso, M.; Hasegawa, A. Glycoconjugate J. 1996, 13, 241.
16. (b) Cao, S.; Meunier, S. J.; Andersson, F. O.; Letellier, M.; Roy, R. Tetrahedron: Asymmetry, 1994, 5, 2303.
17. 14. (a) Martin, T. J.; Schmidt, R. R. Tetrahedron Lett., 1992, 33, 6123.
18. (b) Greilich, U.; Brescello, R.; Jung, K.-H.; Schmidt, R. R. Liebigs Ann., 1996, 663.
19. C-1-H-3″ax ∼0 Hz. Full descriptions of NMR data are given in EXPERIMENTAL.
20. 16. Debenham, J. S.; Madson, R.; Roberts, C.; Fraser-Reid, B. J. Am. Chem. Soc., 1995, 117, 3302.
21. 17. Castro-Palomino, J. C.; Schmidt, R. R. Tetrahedron Lett. 1995, 36, 5343.